Benzenesulfonyl chloride → 1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1515929Notes

Reaction equation

HRID 1515929 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[CH:3]=[CH:2]1.[OH-].[Na+].[C:12]1([S:18](Cl)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[C:12]1([S:18]([N:1]2[C:9]3=[N:8][CH:7]=[CH:6][CH:5]=[C:4]3[CH:3]=[CH:2]2)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 14798Sodium Hydroxide

Product 1

HCID 8520781-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridineYield 89.2%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 7-azaindole (10 g, 84.6 mmol) and tetrabutylammonium bromide (0.81 g, 2.53 mmol) in dichloromethane (211 mL, 0.4 M) at 0° C. was treated with powdered sodium hydroxide (10.15 g, 253.9 mmol). This solution was stirred at 0° C. for 10 min, it was then slowly treated with benzenesulfonyl chloride (16.3 mL, 126.9 mmol). The reaction was allowed to gradually warm to 25° C. and was stirred for 16 h. At this time, the resulting solids were removed by filtration and were washed with dichloromethane (2×50 mL). The filtrate was concentrated in vacuo to afford a yellow solid which was dried under high vacuum for 30 min. At this time, the solids were triturated with hexanes (3×50 mL) to afford 1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridine (19.5 g, 89.2%) as a light yellow solid: 1H NMR (400 MHz, d6-DMSO) δ ppm 8.38 (dd, 1H, J1=4.5 Hz, J2=1.2 Hz), 8.12 (d, 2H, J=7.8 Hz), 8.05 (dd, 1H, J1=7.8 Hz, J2=1.8 Hz), 7.93 (d, 1H, J=3.9 Hz), 7.74-7.59 (m, 3H), 7.32-7.28 (m, 1H), 6.84 (d, 1H, J=3.9 Hz).

Workup

  1. temperatureto gradually warm to 25° C.
  2. stirringwas stirred for 16 h
  3. customAt this time, the resulting solids were removed by filtration
  4. washwere washed with dichloromethane (2×50 mL)
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto afford a yellow solid which
  7. customwas dried under high vacuum for 30 min
  8. customAt this time, the solids were triturated with hexanes (3×50 mL)

Sources & evidence

ORD record
ord-feb392d5bc594e9ab9db16beda68fcbd
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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